But that might prove to be a bit more difficult than expected, in light of his "friend" posting a video of Monahan drunk and naked while on vacation in India to Facebook.

The video, which shows Monahan completely nude and slurring, was picked up by Gawker's Sam Biddle and later, BetaBeat.

Monahan and his two friends arrived at the private beach resort Surya Samudra a couple of days ahead of Dave McClure's "Geeks On a Plane" tour, where Monahan is a mentor, according to BetaBeat.

But it turns out that around the same time Monahan was drinking on the beach, he sent out an email to investors about his discussions with "stakeholders" at companies like Facebook, Salesforce, and Oracle, some of which "fell flat." He also wrote about his upcoming meetings with Google and Yahoo, according to an email leaked to BetaBeat.

In the email, Monahan wrote that AlphaBoost had received a verbal offer for a deal that was expected to materialize in mid-March. As part of that deal, the acquiring company would exclusively license AlphaBoost's technology, AlphaBoost would shut down, and the whole team would join the acquiring company.

As of January 31, AlphaBoost had four months of runway left with clients spending more than $32 million on the platform. As a back-up plan, AlphaBoost intended to meet with investors next month to discuss a potential Series A round.

It may be an expensive lesson learned. We're not sure who looks worse, Monahan, or the jerk-of-a "friend," Inc 30 Under 30 founder Jesse Thomas, who posted the video. Thomas also posted naked photos to Facebook, as if the embarrassing video wasn't enough.

Business Insider has reached out to both McClure and Monahan. We will update this story if we hear back.

UPDATE: We just spoke with McClure about the situation, who won't speak for Thomas and Monahan's judgment at this point, but says theyr'e both smart folks. He says, despite Monahan running around drunk and naked, Monahan's business is still interesting.